EP2046318B1 - Combination of adapalene and benzoyl peroxide for treating inflammatory acne lesions - Google Patents
Combination of adapalene and benzoyl peroxide for treating inflammatory acne lesions Download PDFInfo
- Publication number
- EP2046318B1 EP2046318B1 EP07787478.2A EP07787478A EP2046318B1 EP 2046318 B1 EP2046318 B1 EP 2046318B1 EP 07787478 A EP07787478 A EP 07787478A EP 2046318 B1 EP2046318 B1 EP 2046318B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- adapalene
- bpo
- combination
- benzoyl peroxide
- lesions
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000004342 Benzoyl peroxide Substances 0.000 title claims description 59
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 title claims description 59
- 235000019400 benzoyl peroxide Nutrition 0.000 title claims description 59
- LZCDAPDGXCYOEH-UHFFFAOYSA-N adapalene Chemical compound C1=C(C(O)=O)C=CC2=CC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OC)=CC=C21 LZCDAPDGXCYOEH-UHFFFAOYSA-N 0.000 title claims description 54
- 229960002916 adapalene Drugs 0.000 title claims description 54
- 230000003902 lesion Effects 0.000 title claims description 31
- 206010000496 acne Diseases 0.000 title claims description 29
- 208000002874 Acne Vulgaris Diseases 0.000 title claims description 28
- 230000002757 inflammatory effect Effects 0.000 title claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- 238000011282 treatment Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 8
- 230000000699 topical effect Effects 0.000 claims description 6
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
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- 230000003110 anti-inflammatory effect Effects 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- -1 adapalene salts Chemical class 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
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- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 2
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- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
- 229940043268 2,2,4,4,6,8,8-heptamethylnonane Drugs 0.000 description 1
- 125000005274 4-hydroxybenzoic acid group Chemical class 0.000 description 1
- 206010000501 Acne conglobata Diseases 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 206010054107 Nodule Diseases 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
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- 229940087168 alpha tocopherol Drugs 0.000 description 1
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- 239000003963 antioxidant agent Substances 0.000 description 1
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- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
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- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
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- KUVMKLCGXIYSNH-UHFFFAOYSA-N isopentadecane Natural products CCCCCCCCCCCCC(C)C KUVMKLCGXIYSNH-UHFFFAOYSA-N 0.000 description 1
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- NPCOQXAVBJJZBQ-UHFFFAOYSA-N reduced coenzyme Q9 Natural products COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C(O)=C1OC NPCOQXAVBJJZBQ-UHFFFAOYSA-N 0.000 description 1
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- FWFUWXVFYKCSQA-UHFFFAOYSA-M sodium;2-methyl-2-(prop-2-enoylamino)propane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(C)(C)NC(=O)C=C FWFUWXVFYKCSQA-UHFFFAOYSA-M 0.000 description 1
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Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/327—Peroxy compounds, e.g. hydroperoxides, peroxides, peroxyacids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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- A—HUMAN NECESSITIES
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12152317.9A EP2450035B1 (en) | 2006-07-13 | 2007-07-12 | Combination of adapalene and benzoyl peroxide for treating acne lesions |
| SI200731283T SI2046318T1 (sl) | 2006-07-13 | 2007-07-12 | Kombinacija adaptalena in benzoil peroksida za zdravljenje vnetnih akenskih lezij |
| DK12152317.9T DK2450035T3 (en) | 2006-07-13 | 2007-07-12 | Combination of adapalene and benzoyl peroxide for the treatment of acne lesions |
| PL07787478T PL2046318T3 (pl) | 2006-07-13 | 2007-07-12 | Kombinacja adapalenu i nadtlenku benzoilu do leczenia zapalnych zmian trądzikowych |
| PL12152317T PL2450035T3 (pl) | 2006-07-13 | 2007-07-12 | Połączenie adapalenu i nadtlenku benzoilu do leczenia zmian trądzikowych |
| CY20131100738T CY1114473T1 (el) | 2006-07-13 | 2013-08-28 | Συνδυασμος αδαπαλενης και υπεροξειδιου του βενζοϋλιου για την αγωγη των φλεγμονωδων βλαβων της ακμης |
| CY20191100091T CY1121398T1 (el) | 2006-07-13 | 2019-01-24 | Συνδυασμος αδαπαλενης και υπεροξειδιου του βενζοϋλιου για την αγωγη των βλαβων της ακμης |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0652968A FR2903603B1 (fr) | 2006-07-13 | 2006-07-13 | Combinaison d'adapalene et de peroxyde de benzole dans le traitement de l'acne |
| US83349106P | 2006-07-27 | 2006-07-27 | |
| PCT/EP2007/057207 WO2008006888A1 (en) | 2006-07-13 | 2007-07-12 | Combination of adapalene and benzoyl peroxide for treating acne lesions |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP12152317.9A Division EP2450035B1 (en) | 2006-07-13 | 2007-07-12 | Combination of adapalene and benzoyl peroxide for treating acne lesions |
| EP12152317.9 Division-Into | 2012-01-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP2046318A1 EP2046318A1 (en) | 2009-04-15 |
| EP2046318B1 true EP2046318B1 (en) | 2013-06-05 |
Family
ID=37763873
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP12152317.9A Active EP2450035B1 (en) | 2006-07-13 | 2007-07-12 | Combination of adapalene and benzoyl peroxide for treating acne lesions |
| EP07787478.2A Active EP2046318B1 (en) | 2006-07-13 | 2007-07-12 | Combination of adapalene and benzoyl peroxide for treating inflammatory acne lesions |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP12152317.9A Active EP2450035B1 (en) | 2006-07-13 | 2007-07-12 | Combination of adapalene and benzoyl peroxide for treating acne lesions |
Country Status (23)
| Country | Link |
|---|---|
| US (6) | US8129362B2 (es) |
| EP (2) | EP2450035B1 (es) |
| JP (3) | JP2009542779A (es) |
| KR (3) | KR20160120352A (es) |
| CN (1) | CN101541320B (es) |
| AR (1) | AR061989A1 (es) |
| AU (1) | AU2007274288B2 (es) |
| BR (1) | BRPI0713182A8 (es) |
| CA (1) | CA2656456A1 (es) |
| CO (1) | CO6150136A2 (es) |
| CY (1) | CY1121398T1 (es) |
| DK (2) | DK2450035T3 (es) |
| ES (2) | ES2703505T3 (es) |
| FR (1) | FR2903603B1 (es) |
| HU (1) | HUE043502T2 (es) |
| LT (1) | LT2450035T (es) |
| MX (1) | MX2009000319A (es) |
| PL (2) | PL2046318T3 (es) |
| PT (2) | PT2046318E (es) |
| RU (3) | RU2009104949A (es) |
| SI (2) | SI2450035T1 (es) |
| TR (1) | TR201819658T4 (es) |
| WO (1) | WO2008006888A1 (es) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7820186B2 (en) | 2001-12-21 | 2010-10-26 | Galderma Research & Development | Gel composition for once-daily treatment of common acne comprising a combination of benzoyl peroxide and adapalene and/or adapalene salt |
| FR2910320B1 (fr) | 2006-12-21 | 2009-02-13 | Galderma Res & Dev S N C Snc | Emulsion comprenant au moins un retinoide et du peroxyde de benzole |
| FR2910321B1 (fr) | 2006-12-21 | 2009-07-10 | Galderma Res & Dev S N C Snc | Gel creme comprenant au moins un retinoide et du peroxyde de benzole |
| AR065085A1 (es) | 2007-01-30 | 2009-05-13 | Galderma Res & Dev | Metodo para tratamiento prolongado del acne vulgaris |
| MX2010005516A (es) * | 2007-11-30 | 2010-06-02 | Galderma Res & Dev | Composiciones que comprenden al menos un derivado del acido naftoico, de peroxido de benzoilo y al menos un agente filmogeno. |
| KR20110021888A (ko) * | 2008-05-16 | 2011-03-04 | 갈데르마 리써어치 앤드 디벨로프먼트 | 여드름 관련 질환을 치료하기 위한 치료 요법 |
| MX2012008871A (es) * | 2010-02-09 | 2012-08-31 | Galderma Res & Dev | Composicion dermatologica que comprende combinacion de adapaleno y peroxido de benzoilo para el tratamiento del acne en poblacion no caucasica con reduccion de hiperpigmentacion post-inflamatoria. |
| JP2013527161A (ja) * | 2010-04-29 | 2013-06-27 | ガルデルマ・リサーチ・アンド・デヴェロップメント | アダパレン０．３％による瘢痕の処置方法 |
| FR2969491B1 (fr) * | 2010-12-23 | 2013-07-12 | Galderma Res & Dev | Mousses dermatologiques obtenues a partir d'un gel ou d'une suspension contenant une combinaison d'adapalene et de bpo |
| US8563535B2 (en) * | 2011-03-29 | 2013-10-22 | Kamal Mehta | Combination composition comprising benzoyl peroxide and adapalene |
| CA2870690A1 (en) * | 2012-05-25 | 2013-11-28 | Galderma Research & Development | Treatment of preadolescent moderate acne vulgaris |
| CN105246457B (zh) | 2012-11-20 | 2019-06-07 | 阿勒根公司 | 局部氨苯砜和氨苯砜/阿达帕林组合物及其使用方法 |
| SG10202100745QA (en) * | 2014-04-01 | 2021-02-25 | Galderma Res & Dev | Combination of adapalene and benzoyl peroxide for treating acne scars |
| RU2017105074A (ru) | 2014-07-25 | 2018-08-27 | Галдерма Ресерч Энд Девелопмент | Комбинация адапалена и бензоилпероксида для лечения тяжелой формы акне |
| US20180235924A1 (en) * | 2015-08-20 | 2018-08-23 | Sol-Gel Technologies Ltd. | Compositions for topical application comprising benzoyl peroxide and adapalene |
| JP6679299B2 (ja) * | 2015-12-21 | 2020-04-15 | 第一三共ヘルスケア株式会社 | ニキビ治療用外用医薬組成物 |
| KR101986177B1 (ko) * | 2016-10-31 | 2019-06-05 | (주)동구바이오제약 | 여드름 치료용 약물의 생체이용률을 증진시키는 약학적 조성물 |
| WO2018080284A1 (ko) * | 2016-10-31 | 2018-05-03 | (주)동구바이오제약 | 여드름 치료용 약물의 생체이용률을 증진시키는 약학적 조성물 |
| MX2017003003A (es) * | 2017-03-08 | 2018-09-07 | Centro Int De Cosmiatria S A P I De C V | Composición y método para el tratamiento tópico del acné severo. |
| US20180280340A1 (en) * | 2017-03-30 | 2018-10-04 | Konstantin Zubovskiy | Method of treating and preventing infections |
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| TW203552B (en) * | 1992-02-18 | 1993-04-11 | J Baroody Lloyd | Compositions of clindamycin and benzoyl peroxide for acne treatment |
| FR2727609B1 (fr) | 1994-12-06 | 1997-01-10 | Oreal | Ensemble de distribution pour l'application d'un produit de consistance liquide a pateuse |
| FR2775566B1 (fr) | 1998-03-03 | 2000-05-12 | Oreal | Cupule porte raisin et ensemble de conditionnement pour un produit de maquillage la comportant |
| US6559189B2 (en) * | 1999-04-28 | 2003-05-06 | Regents Of The University Of Michigan | Non-toxic antimicrobial compositions and methods of use |
| FR2806273B1 (fr) | 2000-03-16 | 2002-10-04 | Oreal | Dispositif de conditionnement et d'application d'un produit cosmetique ou de soin |
| US7820186B2 (en) * | 2001-12-21 | 2010-10-26 | Galderma Research & Development | Gel composition for once-daily treatment of common acne comprising a combination of benzoyl peroxide and adapalene and/or adapalene salt |
| FR2833841B1 (fr) * | 2001-12-21 | 2005-07-22 | Galderma Res & Dev | Gel comprenant au moins un retinoide et du peroxyde de benzoyle |
| FR2837101B1 (fr) | 2002-03-12 | 2004-07-02 | Galderma Res & Dev | Utilisation de l'acide 6-[1-adamantyl)-4-methoxyphenyl]-2- naphthoique pour le traitement de desordres dermatologiques |
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| WO2007132134A2 (fr) * | 2006-05-17 | 2007-11-22 | Galderma Research & Development | Compositions comprenant au moins un dérivé de l'acide naphtoïque et du péroxyde de benzoyle, leurs procédés de préparation, et leurs utilisations |
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